Brand new here, although I've lurked here off and on for the last few years. Finally wanted to share my experience as first time cross dressing and my encounter since I don't have anyone else to share it with. Not sure how good my writing is so please bare with me.

Anyways, I'm a 24 year-old that has always had a fantasy of being with an older man and having him dress me up and role play that I was the "naughty" daughter that he would introduce me to sex. I've had this fantasy for the last few years but never had a chance or the guts to fulfill it though. For me it was always the idea of the age difference and "role reversal" that did it for me. As far as myself, I'm definitely your average college guy with a girlfriend that no one would suspect as having these fantasies.

After feeling really horny, I made a few ads on some websites and actually didn't have any luck finding anyone. Most of the guys simply wanted to get laid and didn't care to discuss my fantasies or theirs, eventually though I started talking to this guy that seemed to fit me well. He was interested in everything I was and after many long talks I came to the conclusion that he wasn't crazy...

After a lot of talking we agreed to meet up one night at his place and just see what I was comfortable with. Prior to this, I had only messed around with a friend when I was younger but was too scared at the time to really enjoy any of the oral or touching that we had done. I was pretty nervous when I arrived at his house but he was very nice and we had a beer or two. I made it known too him that I wanted him to make the first initiation and before I knew it he was grabbing my ass. My hands started to wonder and before I knew it I was feeling his very hard member through his pants. He couldn't take it for long and removed his pants and sat on the couch. I gladly began sucking him off but was surprised at how little I could fit of him in my mouth, he wasn't long but was very thick. He enjoyed it though and I could tell from his moans that I wasn't that bad. Eventually my pants came off and I gave him a hand job so I could watch him cum, this for whatever reason was really exciting to me since I knew that I had caused that from him. After he came, he took me in his mouth and told me to cum and I gladly did. He asked if I was ready to fuck him and I said "no" due too still being nervous and it was already getting late.

After a week or two, we continued to talk but our schedules weren't quite working out so we didn't get too meet up. One night though while chatting online, and having a few beers and being especially horny I sugested that he get us a hotel room. For some reason, I always imagined getting fucked there and felt comfortable. I said this half-jokingly and before I knew it, he had a room booked. I met him in the parking lot and we walked up too his room. It was pretty nice, he had some beer in the fridge and I had brought a backpack in with some supplies.

For whatever reason, I wasn't feeling too nervous and told him that I wanted to take a shower since I really wasn't expecting this too happen. He laid out my clothes for me which included a short white top ( I have no idea what it's called but it looked good), a plaid skirt with a belt and a white thong. After using the restroom and jumping in the shower I got out and it finally hit me. All of a sudden I was terribly nervous. After smoking a cigarette in the bathroom, and looking at the clothes I was about too put on he knocked and asked if everything was ok. I told him that I was just finishing up and would be out shortly. I must have been in there for a while without even realizing it. Anyways, I finally decided that yes this is what I wanted to do and too just go for it. I knew with him that if I was uncomfortable with anything that he would not push it and be ok with it.

After fiddling with the damn skirt, it took a few minutes to figure out how the hell the belt was supposed to work with it and another cigarette. I finally walked out of the bathroom. He jumped up from the bed, and had been watching tv. He came over to me and handed me a beer which I gladly accepted and took a few swigs of. At this point, I had become more comfortable and began too take on my new "feminine" role. I showed off for him by acting feminine and teasing me. He was obviously turned on and kept complimenting me on how great I looked. I turned around from him to keep teasing and before I knew it he had came up from behind me. He rubbed his dick on my ass and I gladly pressed into him as he kissed on my neck.

After some grinding on him he turned me around and we began too kiss. I'm still not sure If I enjoyed it or not, I guess it was just different kissing a man instead of a woman but I had fun. After a little while of that and him slowly going up my skirt I couldn't take it anymore and dropped down too my knees. After unbuckling his pants, I could see his hard dick through his boxer briefs. I teased him a little before I pulled down his underwear. I then began too give him head, licking and stroking him. He began moaning and before I knew it he had lifted me up and gently put me on the bed. At this point I was so turned on that I couldn't keep my hands off him and kept jacking him off as he began to undo my top and suck on my nipples. At the same time his hands were going up my skirt gently teasing my penis, which barely could stay in the small panties that he had given me. He slowly pulled off my panties and began to slowly suck me off. At this point I was in heaven and he stopped. I couldn't figure out why and didn't want it too but he got up and grabbed some lube. Before this I had done some anal play with myself but only fingers and some small objects. He continued to suck me off while he slowly entered a finger, then two.

It took a while for me to relax, but was enjoying the dual sensation of getting head and the fingers. Finally I spoke up and told him that I wanted him to fuck me. He pulled out a condom and I told him to lay down. After he put it down I tried to get on top of him but was either too nervous or too tight and he couldn't get in me. At this point I thought that it wasn't going to work at all. He was very wide but he told me too get on all fours and too try that. After more fingers and lube he finally entered me very slowly. Although it didn't hurt that much, it was definitely a strange feeling. Luckily he took it very slow and before I knew it he was all the way in. After sensing me being comfortable he began to pick up the pace, at this point I began moaning like a little bitch and buried my head in the pillows. He fucked me for a few minutes pretty hard, all I could do was moan and take it. Eventually he flipped me over and wanted me to flip my legs up. I did so but that position was way too deep for me, thankfully he was slow. After that, I had him take off the condom and began stroking him off, then had him cum on my chest which was a lot of fun. He then gave me a great blowjob and I came in his mouth.

After a shower, I thanked him with another bj and he did the same too me. I don't know if I'll ever do this again. But writing this really wants me too! I hope you guys enjoyed.

Thanks for the kind words everyone, I'm glad you all enjoyed as much as I did writing it. I'm not the best writer, so hearing that it was good will only encourage me too keep posting.

I'm still wondering if I'll ever try it again, it was fun and I'm sure the next time will be better due too the lack of nerves. My next fantasy is too be with an older couple, man and woman, who knows maybe work in the cross-dressing... I have way too much time too think about these...

Well simply writing this out has awoken something in me. I decided I'm going to go through with it again with the same guy. We hadn't talked in a while but I sent him an email and he was more than happy to play again... too say the least.

We talked for a few hours online, leaving us both very horny and ready to meet as soon as possible. We talked about our fantasies and it seems that he wants me too dress up a little more, meaning he's going to get me a wig and a new outfit. Another cool thing is I've agreed to let him be a little more "aggressive", meaning he knows the limits but can take the initiative and I'll be fine with it.

So I'm tasked to pick out a new outfit for me to wear. Some help would be appreciated, I'm 5'8, about 150lbs, athletic/slim build. We've already done the schoolgirl outfit the first time so I'm looking on suggestions on what type of outfit you would pick out in my shoes. I'm leaning towards a black set that includes a halter top and a short black skirt with a thong. He's looking for a white outfit with some fishnet leggings, but I'm not really sure what that would look like.

Are there any suggestions? Also, when wearing thongs, how can I find the right size? I have large testicles, not bragging or anything, and the thong fit great along my waist but I couldn't keep them from popping out... lol. Another thing is, how can I convert my waist of 32 inches to a woman's to get a skirt to fit?

Anyways, I look forward to any suggestions or websites to help me make the decision. Fantasizing about it is almost as fun as making it happen. I'll keep you updated and write the details of the encounter also if anyone is interested.

Another thing is, how can I convert my waist of 32 inches to a woman's to get a skirt to fit?

Why not just stop in to a friendly store and try on a few skirts? I've tried on women's things in a number of department stores; they have no problem with it, and it's quite exhilarating (for me, anyway )!

I enjoyed it very much. I'm a middle aged man and have never had sex with another man, but have fantasized about it many times. I put myself in your position during the story and now I am soo hard and in need a man.

my first time crossdressing was mostly done to piss people off when i played in a punk band in high school. my dad saw me in fishnet stockings, a purple cocktail dress and converse chucks. luckily he just shook his head and walked away.
my first time with a CD was in highschool(we were both 18) he was this kind of obnoxious kid but pretty hot when he dressed himself up. he had a girlfriend and would always tell me how they fucked all the time. anyway, we had to wait until his dad left, then i pulled up his skirt and pulled down his stockings and sucked his dick. he did the same to me, and he ended up shooting cum all over my face on accident. when i was cleaning up in the sink i saw his wig in there and the whole thing seemed like a bad idea after the fact, but hell, when you'rei 18 everything sounds like a great idea.

Well simply writing this out has awoken something in me. I decided I'm going to go through with it again with the same guy. We hadn't talked in a while but I sent him an email and he was more than happy to play again... too say the least.

We talked for a few hours online, leaving us both very horny and ready to meet as soon as possible. We talked about our fantasies and it seems that he wants me too dress up a little more, meaning he's going to get me a wig and a new outfit. Another cool thing is I've agreed to let him be a little more "aggressive", meaning he knows the limits but can take the initiative and I'll be fine with it.

So I'm tasked to pick out a new outfit for me to wear. Some help would be appreciated, I'm 5'8, about 150lbs, athletic/slim build. We've already done the schoolgirl outfit the first time so I'm looking on suggestions on what type of outfit you would pick out in my shoes. I'm leaning towards a black set that includes a halter top and a short black skirt with a thong. He's looking for a white outfit with some fishnet leggings, but I'm not really sure what that would look like.

Are there any suggestions? Also, when wearing thongs, how can I find the right size? I have large testicles, not bragging or anything, and the thong fit great along my waist but I couldn't keep them from popping out... lol. Another thing is, how can I convert my waist of 32 inches to a woman's to get a skirt to fit?

Anyways, I look forward to any suggestions or websites to help me make the decision. Fantasizing about it is almost as fun as making it happen. I'll keep you updated and write the details of the encounter also if anyone is interested.

love your posts iam hard just thinking about your next meet. I too have started to dress crossdresser.com is a good site many of them give size charts. I would not feel ok asking a store clerk help for girls sizes. i vote for the black shirt & halter.

Brand new here, although I've lurked here off and on for the last few years. Finally wanted to share my experience as first time cross dressing and my encounter since I don't have anyone else to share it with. Not sure how good my writing is so please bare with me.

Anyways, I'm a 24 year-old that has always had a fantasy of being with an older man and having him dress me up and role play that I was the "naughty" daughter that he would introduce me to sex. I've had this fantasy for the last few years but never had a chance or the guts to fulfill it though. For me it was always the idea of the age difference and "role reversal" that did it for me. As far as myself, I'm definitely your average college guy with a girlfriend that no one would suspect as having these fantasies.

After feeling really horny, I made a few ads on some websites and actually didn't have any luck finding anyone. Most of the guys simply wanted to get laid and didn't care to discuss my fantasies or theirs, eventually though I started talking to this guy that seemed to fit me well. He was interested in everything I was and after many long talks I came to the conclusion that he wasn't crazy...

After a lot of talking we agreed to meet up one night at his place and just see what I was comfortable with. Prior to this, I had only messed around with a friend when I was younger but was too scared at the time to really enjoy any of the oral or touching that we had done. I was pretty nervous when I arrived at his house but he was very nice and we had a beer or two. I made it known too him that I wanted him to make the first initiation and before I knew it he was grabbing my ass. My hands started to wonder and before I knew it I was feeling his very hard member through his pants. He couldn't take it for long and removed his pants and sat on the couch. I gladly began sucking him off but was surprised at how little I could fit of him in my mouth, he wasn't long but was very thick. He enjoyed it though and I could tell from his moans that I wasn't that bad. Eventually my pants came off and I gave him a hand job so I could watch him cum, this for whatever reason was really exciting to me since I knew that I had caused that from him. After he came, he took me in his mouth and told me to cum and I gladly did. He asked if I was ready to fuck him and I said "no" due too still being nervous and it was already getting late.

Continued in next post... Not sure how much I can write.

I have exactly the same desire for older/more dom men too, I know just how you feel. Short, black leather/PVC skirts always do it for me, very shiny and smooth, feel great against the skin
xx

I am a closet cross dresser but I did get brave last Saturday. I had to drive to Seattle and on the way back I bought a skirt and a red thong and changed in the car. Then drove to the rest stop in Marysville where I made my first public appearence. Got back into the car and headed home hoping that a trucker would like my legs and want to see and do more. As luck would have it all the trucks were headed south and I was going north. However, the feeling of my bare legs exposed and a slight exposure of red panty gave me the "rush" of letting the woman in me escape even if only for a few hours.

I am a closet cross dresser but I did get brave last Saturday. I had to drive to Seattle and on the way back I bought a skirt and a red thong and changed in the car. Then drove to the rest stop in Marysville where I made my first public appearence. Got back into the car and headed home hoping that a trucker would like my legs and want to see and do more. As luck would have it all the trucks were headed south and I was going north. However, the feeling of my bare legs exposed and a slight exposure of red panty gave me the "rush" of letting the woman in me escape even if only for a few hours.

wow! Go you! That was certainly brave of you!

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